Synthesis and stereochemistry of some heterocyclic saturated compounds based on l-p-nitrophenylserinol skeleton (I). Ring-chain tautomerism of some Schiff bases of l-p-nitrophenylserinol

Tetrahedron

Volumn 53, Issue 5, 1997, Pages 1873-1890

  Darabantu, Mircea ^a   Plé, Gerard ^b   Mager, Sorin ^a   Cotora, Eleonora ^c   Gaina, Luiza ^a   Costas, Loredana ^a   Mates, Adrian ^a  

^a BABE BOLYAI UNIVERSITY   (Romania)

^b UNIVERSITÉ DE ROUEN   (France)

^c NATIONAL INSTITUTE FOR CHEMICAL PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (Romania)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; OXAZOLIDINONE DERIVATIVE; SCHIFF BASE;

ARTICLE; CONFORMATION; CYCLIZATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031550587     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)01104-0     Document Type: Article

References (31)

1. 1. Baldwin, J.; J. Chem. Soc., Chem. Commun. 1976, 734
2. 2. Valters, R.; Flitsch, W., Ring-Chain Tautomerism, Plenum Press, New-York, 1985
3. 3. Fûlõp, F.; Pihlaja, J.; Mattinen, J.; Bernáth, G., J. Org. Chem., 1987, 52, 3821
4. 4. Fûlõp, F.; Pihlaja, K.; Neuvonen, K.; Bernáth, G.; Argay, G.; Kálmán, A., J.Org. Chem., 1993, 58, 1967-1969
5. 5. Pihlaja, K.; Parkkinen, A.; Lönnberg, H., J. Chem. Soc., Perkin Trans 2, 1983, 1223
6. 6. Parkkinen, A.; Mattinen, J.; Lönnberg, J.; Pihlaja, K., J. Chem. Soc., Perkin Trans.2 1988, 827
7. 7. Hagopian, L.; Fife, T., H., J. Am. Chem. Soc., 1968, 90, 1007
8. 8. Ridell, F., G.; Arumugam, S.; Fûlõp, F.; Bernáth, G., Tetrahedron, 1992, 48, 4979-4983
9. 9. Umezawa, S.; Suami, T., Bull. Chem. Soc. Japan, 1954, 27, 477
10. 10. Suami, T.; Uchide, J.; Umezawa, S., Bull. Chem. Soc. Japan, 1956, 29, 979-985
11. 11. Collins, R., J., J. Pharm. Pharmacol., 1952, 4, 963
12. 12. Pedrazzoli, A.; Tricerri, S., Helv. Chim. Acta, 1956, 39, 965-976
13. 13. Edgerton, W., H.; Fisher, J., R.; Moersch, J., W., J. Org. Chem., 1954, 19, 593
14. 14. Edgerton, W., H.; Fisher, J., R.; Moersch, J., W., J.Am. Chem. Soc., 1957, 79, 6487-6490
15. 15. Nagawa, M., Ann. Rept. Takamine Lab., 1955, 7, 1-3 (Chem.Abstr., 1956, 50, 14764c)
16. 15. Nagawa, M., Ann. Rept. Takamine Lab., 1955, 7, 1-3 (Chem.Abstr., 1956, 50, 14764c)
17. 16. Haak, E.; Dimroth, H.; Hagedorn, A.; Heimberger, W.; Peshke, W., U.S.Pat., 2,957,916 ; (Chem.Abstr., 1961, 55, P93493i)
18. 16. Haak, E.; Dimroth, H.; Hagedorn, A.; Heimberger, W.; Peshke, W., U.S.Pat., 2,957,916 ; (Chem.Abstr., 1961, 55, P93493i)
19. 17. Darabantu, M.; Mager, S.; Plé, G.; Puscas, C., Heterocycles, 1995, 41, (10), 2327-2356
20. 18. Bergmann, E., Chem. Rev., 1953, 53, 309-352
21. 19a-c. (19a) Potapov, V., M.; Dem'yanovich, V., M.; Zaitsev, V., P.; Sharipova, S., Kh., Zh. Org. Khim., 1990, 26, (12), 2574-2579;
22. see also the related data: (19b) Chenevert, R.; Voyer, N., Synth. Comm., 1985, 981-982;
23. (19c) Sohár, P.; Mikite, Gy.; Pelczer, I.; Kovács, Á.; Kis-Tamás, A., Org. Magn. Reson., 1984, 22, (11), 710-716
24. 20. Paukstelis, J., V.; Lambing, L., L., Tetrahedron Lett., 1970, 299.
25. 21. Okamoto, Y.; Brown, J., J. Am. Chem. Soc., 1958, 80, 4969
26. 22. Brown, J.; Okamoto, Y., J. Am. Chem. Soc., 1958, 80, 4979
27. 23. Crabb, T., A.; Hall, M., J.; Williams, R., O., Tetrahedron, 1973, 29, 3389-3398
28. 24. Darabantu, M.; Mager, S.; Puscas, C; Ple, G.; Bogdan, M.; Cotora, E.; Bratu, I., Rev. Rom. Chim. 1994, 39, (8), 955-966
29. 25. Friebolin, H., Basic One and Two-Dimensional NMR Spectroscopy; VCH Verlagsgesellschaft mbH, D-6940 Weinheim (Federal Republic of Germany), 1991; pp 77
30. 26. Alva Astudillo; Chokotko, M., E.; Jarvis, N., C., J.; Johnson, T., C.; Lewis, C., D.; Donell, P., D., Mc., Tetrahedron, 1985, 41, 5919
31. 27. Bergmann, E.; Resnik, H.; J. Chem. Soc., 1956, 1662-1665